Ethanol → HCID 67396484, compound

HRID 1426791Notes

Reaction equation

HRID 1426791 reaction equation
[F:1][C:2]1[C:3]([CH2:26][N:27](C)[C:28](=O)[O:29][C:30]([CH3:33])(C)C)=[CH:4][N:5]([S:17]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[C:6]=1[C:7]1[C:8]([C:13]([F:16])([F:15])[F:14])=[N:9][CH:10]=[CH:11][CH:12]=1.[C:36]([O:39]CC)(=[O:38])[CH3:37].Cl.C([OH:45])C>>[C:30]([OH:29])(=[O:45])/[CH:33]=[CH:37]/[C:36]([OH:39])=[O:38].[F:1][C:2]1[C:3]([CH2:26][NH:27][CH3:28])=[CH:4][N:5]([S:17]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[C:6]=1[C:7]1[C:8]([C:13]([F:16])([F:15])[F:14])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 67395988HCID 67395988, compound

Product 1

HCID 67396484HCID 67396484, compound

Procedure

To a solution of tert-butyl ({4-fluoro-1-(pyridin-3-ylsulfonyl)-5-[2-(trifluoromethyl)pyridin-3-yl]-1H-pyrrol-3-yl}methyl)methylcarbamate (506 mg) in ethanol (5 mL) was added 4 mol/L hydrogen chloride-ethyl acetate solution (5 mL), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate) to give the title compound as a free base (307 mg). To a solution of the obtained free base (229 mg) in ethyl acetate (3 mL) was added a solution of fumaric acid (65.1 mg) in ethanol (3 mL), and the mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from ethanol to give the title compound as a white solid (yield 209 mg, 39%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionSaturated aqueous sodium hydrogen carbonate solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-c6ba729c55524fb0923a27fa968e1afb
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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